


Left-handed Sweetheart

by Hatsonhamburgers



Category: Supernatural
Genre: 10 things I Hate About You - Freeform, 69 (Sex Position), Alternate Universe - High School, Anal Sex, Awkward Blow Jobs, Awkward Flirting, Boys Kissing, Butt Sex, First Time, Fluff and Smut, Hormones, M/M, Prom, References to Shakespeare, Swing Dancing, Teen Angst, Tumblr: deancas-sweetheart, Valentine's Day Fluff, Virgin Castiel, Virgin Dean, and none for Gretchen Weiners, basically virgin everyone, charlie and dorothy are lesbian power couple, gratuitous use of Victorian euphemisms for gay, lgbtq studies, sit on my face
Language: English
Status: Completed
Published: 2017-02-15
Updated: 2017-02-15
Packaged: 2018-09-24 16:22:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 17,217
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9770159
Author URL: https://archiveofourown.org/users/Hatsonhamburgers/pseuds/Hatsonhamburgers
Summary: It's Valentine's Day at Lawrence High, and a Cas is salty about the whole thing.  Until he gets a carnation from a secret admirer, that is.Will Cas find out who it is?  Will he quit being bitter about love??  Will it be Dean Winchester???  Will there be hot sexual situations????All the answers to these questions (plus ones you didn't even ask) and more!





	1. Chapter 1

**Author's Note:**

> Here's a thing!!!!!!!
> 
> I'm not a fan of Valentine's Day. Except the part where there's candy for sale the day after :D
> 
> But these two idiots make me believe in love <3<3<3

Castiel pushed his glasses up the bridge of his nose for the millionth time. 

“I just don’t see why everyone cares so much about this stupid, meaningless tradition. And I’m not exactly sure how buying cheap dyed carnations for each other pays homage to the martyrdom of a third century saint”

Charlie chuckled but continued to fill out the slip of paper to order a red carnation for her girlfriend Dorothy. “You’re just mad because you haven’t gotten one the last three years. Besides, it’s a school fundraiser.”

“Yeah,” Cas huffed with an eyeroll, “to benefit the Football program. Like they need it. It would be better suited to donate the money to the library. They are in dire need of newer non-fiction and maybe some renovations.”

Charlie waved the paper back and forth to dry the ink before handing it to the cheerleader behind the table with a five dollar bill and a wink. The cheerleader blushed, obviously flattered, and got Charlie her change. 

“Besides,” Charlie continued, linking her arm with Cas’s as she lead him away from the table, “it’s fun. Why don’t you quit it with the pity party and buy one for someone else? It doesn’t have to be a pink or red one, buy a white one for a friend. It would totally make their day.” She nudged Cas with her elbow. 

Cas’s frown deepened. “Because that worked out so well last time.”

Charlie sighed. “You’re hopeless. But I know this angst exterior is just a cover for the mushy romantic that you are under all that trench coat.”

“I’m 18, I think I’m entitled to a little angst,” he shot back. “Besides, who do I know who’d want a flower from me anyway? Except you maybe- and my presence in your life is gift enough.”

Charlie slung her arm around his shoulders and gave him a half hug, knocking his glasses back down his nose. “Terrible puns aside, I gotta get to class- you be nice to yourself. I can’t tolerate it when people are mean to my friends.”

She finally got a smile out of him, and waved as she skipped off down the hall to class.

Cas sighed and turned to head back the way he came and ran directly into a large figure in a letterman jacket. 

“Ommph!” he grunted as he hit the floor. Papers scattered everywhere and people stopped to stare. He ignored them and began to gather his items. If he was lucky, the jock would just walk away and not try and start some shit.

“I am so sorry, oh crap, here let me help you.” 

Cas looked up to see who the frantic voice belonged to, hoping that his ears were deceiving him and it was _not_ Dean Winchester, quarterback of the Lawrence High football team. _Oh fuck._ As if his day couldn’t get any worse, the hottest guy in the whole school was about 8 inches from his face on all fours helping him pick up pages of his essay about being LGBTQ in a modern context versus the Victorian era. _Dandy._ Cas had to stifle the burst of nervous laughter trying to force its way out of his throat. 

Dean was holding a few pages and sitting back on his knees. His brows were furrowed as he skimmed the words. Cas snatched them away quickly and mumbled a thanks.

Dean seemed to freeze for a second before shaking his head slightly and turning on his 1000 watt smile at Cas. “So you’re in Singer’s Gender Studies class, huh?”

Cas nodded and waited for the insults to fly. When Dean was quiet, Cas finally looked up at him. The man was focused directly on Cas, his eyes wide and innocent, green and bright. _One could get lost in those eyes,_ the traitorous horndog in his mind supplied. He realized he was staring and looked back down at the sheaf of papers in his hand, shuffling them nervously. 

“Uh, yeah. I’m actually going to college to study Anthropology and Sociology. So, um I figured, um…” He blushed deeply and stuffed the papers back into the folder they had flown out of. He prayed that Dean hadn’t seen the subject of the essay- he wasn’t exactly out in school and knew some of the football players to be bigots. It would be his luck to be tormented for the rest of senior year by this Adonis. _Wait, what?_

Dean’s eyebrows shot up. “Really? That’s cool. You planning on going to KU? I hear they have a pretty good Anthropology program.”

Cas tilted his head slightly. This was interesting. This jock knew something about Anthropology? He nodded slowly. “Yeah, they do. I like the idea of staying close to home because-” Why was he telling this virtual stranger about his family problems? “Nevermind.” He shook his head. “I need to get to class. Thanks for helping me pick up- yeah. Thanks.” 

Castiel suddenly became aware of his surroundings. He was sitting on the floor of the English hall with the quarterback of the football team, arguably the most popular boy in school, while people walked around them on the way to class. A few people stared, but no one said anything and moved along as if they weren’t there. As if it were a normal occurrence for a nerd and a jock to be talking intimately on the floor at 9am on a Thursday. He scrambled up and gave Dean a half-smile as he scuttled off to class. He could feel the green eyes follow him down the hall until he disappeared through the door. 

Cas slid into his seat next to Kevin Tran and dropped his head on the desk with a thump and a groan.

“Hey who pissed in your cornflakes?” Kevin asked, his voice teasing, “they wouldn’t happen to be tall, dark, and wearing a letterman jacket, would they?”

Cas grimaced and turned his head to look at Kevin. “You saw that?”

Kevin smirked. “I think the whole school saw that. It might actually help your social standing.”

“Hardly,” Cas huffed. “Most likely it will help me be the subject of torment by the whole football team. There’s no way Dean Winchester will get away with talking to _me_ without his friends fucking with him. And, of course, the school bullying policy is a ‘trickle down’ effect, so it will all land on me somehow.”

“Is this about Valentine’s Day?” Kevin asked seriously. “Because that was two years ago, and no one remembers it anyway.”

“You’re not making your point by bringing it up now,” Cas spat.

Kevin threw up his ‘look out we got a badass over here’ hands and shook his head. “My bad, won’t bring it up again.”

Cas sighed and slumped down in his seat, resting his head on the backrest. “No, I’m sorry, you’re right, I should let it go. But it was kind of one of those defining moments where I decided to stay closeted was easier than facing ridicule. I just don’t like remembering the most humiliating moment of my life.”

Two years ago, Cas had made a bold move and bought a pink carnation for Balthazar, a guy he had a crush on. He was almost positive that the affection was mutual, but when the cheerleaders who sold the flowers, specifically Naomi, saw who it was for, they told basically the whole school. He had tried to play it off like it was a joke, but before he could explain, Balthazar got wind of the rumor and was really upset. Cas was at first sure it was because his advances were unwelcome, but Balthazar later revealed that Cas making a joke about it was what really hurt him. They fell out, and Cas flew under the radar after that. The one time he had ever liked anyone, and he had fucked it up royally. Maybe the school had forgotten about the incident, especially when Balthazar moved back to England, but it still felt fresh to Cas. 

Mr. Singer walked into class and set his ever-present mug of coffee down with a clunk. He grumbled under his breath and rearranged his papers with a moody frown on his face. Cas and Kevin smiled at each other- Mr. Singer was especially poetic when he was grumpy, and swore a lot. It seemed to be the teacher’s way of working out frustration. He never swore at the kids or directed his ire at them, but he would go off on these long tirades about societal norms that were destroying America’s youth. Today it looked like it was going to be a doozy. Cas couldn’t wait.

Mr. Singer began to call roll. He was only halfway down the roster when he threw down his pen and put his hands on his hips. He shook his head at the floor and finally met the eyes of his students.

“You know what gets me? I mean you know what really pisses me off more than anything? I mean, more than anything today- tomorrow it’ll be something totally different- but today I am so goddamn pissed…” He shook his head at the floor again and cleared his throat. Cas was surprised to see the teacher’s eye redden, as if he were about to cry. _That’s new._

“Masculinity is a prison and most folks don’t even know they’re in there. And I’m not just talking about men. Women can be misogynists too. So can non-binary folks. Labeling someone as ‘macho’ or ‘manly’ and expecting them to be a certain way- to treat women a certain way- to treat other men a certain way- is damaging. To women, men, non-binary folks, and especially the poor kid who was labeled as such.”

Cas swore he saw Mr. Singer’s eyes dart his way. _Oh fuck, what’s this about?_

The teacher continued, straightened up, and set his shoulders, blinking back the display of emotion. “Just so ya’ll know, I’m not going to cry in front of you; not because it’s ‘unmanly’ but because it’s too early in the day and dammit I got to make it to two o’clock without gettin’ snot all over my shirt.”

The class chuckled, not unkindly. They were used to Mr. Singer’s passion and compassion overwhelming him. It was what made him such an effective teacher. His subject was an emotional one, and he felt so deeply about it. On more than one occasion, a student would break down and he had several safety measures in place to help them out. The corner of the room had a carpet and several large pillows in case someone needed some space, there were several stuffed animals for hugging if human contact made you uncomfortable, and sometimes (and this was Cas’s favorite thing) when someone was upset and needed to be grounded, the class would stand in a tight circle, shoulder to shoulder, and allow the person to be part of the circle and not the middle; letting the feel that they were part of a greater whole and not singled out or alone. Mr. Singer’s class was the main reason Cas wanted to get a degree in that field. 

“It’s just…” Mr. Singer took a deep breath. “It’s just when someone important to you is afraid to be who they are because of pressure from so-called friends, you want to shake them and let them see that there is so much more to them than the labels society puts on them. That their misguided father-” he stopped himself. And wiped a hand down his face, seeming to collect himself. 

“Okay now that that’s out of the way, let’s circle the desks and see where everyone is on their essays. The time is now, people, if you are including these in college applications, the End is Nigh and we need them sent soon.”

There was a squeak of furniture and light chatter as the students started pushing their desks into place. Cas hadn’t moved. He was deep in thought. _What did Mr. Singer mean by “someone important”? It clearly was something that just happened…_ Cas has a sense of foreboding roll through his stomach. He knew that in some way it had to do with him, but although he had a good rapport with Mr. Singer, lhe could hardly be considered “someone important” to the man. Kevin cleared his throat and Cas jumped up to move his desk into the circle.


	2. Chapter 2

**Notes for the Chapter:**

> I forgot to mention that I neglected to beta this masterpiece of ridiculousness :)

Cas flipped up his collar against the cold February air. The wind was howling, but still there was no snow. It had been snow skies for several days, but it was nothing more than idle threats. He would have liked a little snow for Christmas- it always made his sister Anna happy when they were little- but it had been stubbornly 52 degrees all January. His brother Gabe had thought it was hilarious and wore a ‘Global Warming is a Myth, Merry Christmas!’ tee-shirt that he screen printed just for the occasion. Cas failed to see the humor in it. He also failed to see the humor in it when Gabe wore it weekly all the way into February. 

Charlie was parked near the back; a tell-tale sign that she had been late to school. Cas wrapped his trench coat tighter around himself and wished he had broken down and wore the new down jacket Michael got him for Christmas. He heard his name from behind and footsteps approaching.

“Hey, um, Cas?”

Of course, it was Dean Fucking Winchester jogging toward him, cheeks red from the wind and eyes clear and bright against the overcast sky. 

Cas pushed his glasses up his nose. “Yeah,” he said, impressed his voice sounded so calm.

“I wanted to apologize for running into you earlier. I hope it didn’t mess up your paper.”

Cas shook his head. “Nah, I have it on my laptop so it was no big deal.”

“Oh, okay,” Dean said, shuffling his feet for a minute. They stared at each other for a moment, silent. Cas began to fidget and nearly groaned in relief when Charlie and Dorothy rounded the corner and headed their way. Dean turned to see who it was- he was smiling when he turned back. “I know Charlie, we have World Civ together fourth period. She’s a Star Wars nut. A woman after my own heart.”

“I prefer ‘Star Wars Enthusiast’, thank you very much,” Charlie said brightly as she approached. “And you, Dean Winchester of the Lawrence High jock brigade are a certified _Princess Bride_ nut.”

Dean chuckled and raised a hand. “Guilty. What can I say, I’m a romantic.”

Cas watched the exchange with interest. He didn’t know Dean and Charlie knew each other. Interesting. Cas had a flash of Dean spread out on his couch eating popcorn and pulling Cas over to cuddle with him- _Wait, what?_ He tried to tune back into the conversation but was a bit slow to respond, so he missed a question aimed at him and now they were all staring. Good thing his cheeks were pink from the cold or they would see how hard he was blushing.

“I’m sorry, what?” 

“Ca-as,” Charlie toned, “I asked if you were okay sharing a backseat with Rudy here since he needs a ride.”

Cas’s eyes got huge at the innuendo. Charlie just smiled innocently and Dorothy elbowed her.

“What Charlie means,” Dorothy translated, “is that we are taking Dean to his house first and is that going to make you late or anything.”

Dean had an eyebrow raised in amusement, then smirked at Charlie and rolled his eyes at the bad joke. “I am at least a foot taller than Rudy,” he said, opening the back door to the car. 

Cas was grateful that Dean didn’t catch the whole “backseat” and “needs a ride” part. 

“I’m just impressed you’ve seen the movie,” Charlie retorted good-naturedly.

“Yeah, it’s like part of jock 101: _Friday Night Lights, Rudy,_ and of course, my personal favorite, _The Longest Yard._ ”

Dorothy snorted as they pulled out of the parking lot. “Sandler or Reynolds?”

“Both,” he replied with a grin, “though that was around the time Adam Sandler quit being funny.”

Cas wished he could contribute to the conversation, but his lack of pop culture knowledge left him silent as the others laughed and chatted about 80’s teen romance movies versus 90’s rom coms. He wasn’t sure he understood what “rom com” was.

There was a comfortable silence in the car as Charlie adjusted the radio.

Dean turned to Cas. “You have Gender Studies, right?”

“I thought we had already established that earlier.” Cas inwardly winced at his snarkiness. 

But Dean just chuckled. “Yeah, Uncle Bobby’s something else. He grumpy as fuck, but it’s all to cover the giant marshmallow filling.”

“You’re related?” Cas was wondering how he didn’t know that. Mr. Singer had never mentioned it in class.

“Yeah, he actually has been taking care of me and my little brother Sammy since our parents died. He’s great. Sammy is going to be a civil rights lawyer because of that man. He’s so smart.”

“Your brother?” 

“Yeah,” Dean said warmly, “Sammy’s a genius. He’s gonna help a lot of people.”

“What about you?”

Dean shook his head and looked beyond Cas out the window. “Not for me. I’m better suited to just keep working in Rufus’s auto shop. That’s where we’re going actually.”

“Oh,” Cas said, “is your car okay? Is that why you needed a ride?”

Dean smiled, his eyes sparkling. “Yeah. My Baby doesn’t like the cold sometimes, and I need to give her a tune up before the snow hits.”

“Like the snow is ever going to hit,” Cas smiled with one corner of his mouth. Dean nodded. 

Charlie pulled into the small parking lot at Rufus’s shop and Dean climbed out, waving to Charlie and thanking her. He flashed a smile at Cas and turned and disappeared into the building. He was wearing faded blue jeans, and they were snug against his backside. Cas sighed wistfully.

“Oh my gawd!” Charlie shrieked, “Cas, you devil!”

He snapped his attention to his friend. “What?”

“I mean, get a room you guys,” she said as Dorothy wolf whistled.

“Shut your face,” Cas groaned, “it wasn’t like that. I was just being friendly. Get over it. And don’t tease him in class. I don’t want to get beat up when he has to protect his hetero image.”

“Jesus, Cas, fine,” she surrendered. “And for the record, assuming he’s het because he’s a football player is you jumping to conclusions. He’s being raised by Bobby Singer for Christ sakes. There’s no way he’s a bigot.”

“I guess you’re right,” he sighed, “but whatever, he’s with that girl Lisa, so there’s no way he would be interested-” he stopped himself short, quickly meeting Charlie’s eyes in the rearview mirror. But it was too late. She was giggling and grabbing Dorothy’s shoulder and rocking her back and forth. 

“Oh my god, he _does_ like him! I knew it. I mean I don’t like dudes, not even a little, but damn he’s easy on the eyes.”

Dorothy shrugged. “You’re not wrong.”

Damn, even Dorothy thought he looked good, sorta. In her very Dorothy way, anyway. 

Cas buried his face in his hands. He wasn’t in the mood for this right now. He had homework. He had stuff going on with family. There were things. Important things. But he couldn’t think of them at the moment because he kept picturing the way Dean lit up when he asked about Baby.

_I wish he’d call me Baby._ Jesus he was beginning to sound like one of those cheesy rom com things they were talking about.

“He asked about you in class,” Charlie said casually.

Cas froze and managed to reel himself in before he asked the inevitable question. 

“Oh. What did he say?” he asked blandly.

She grinned manically in the mirror. “He told me about your run-in and said he thought we were friends. I don’t know Cas, it seemed like he wanted to meet you again. One of his teammates could have given him a ride, but he asked me instead.”

“Sometimes a cigar is just a cigar,” Cas said under his breath. 

“What?” She shot back.

“Nothing. I was saying maybe he just needed a ride and you were convenient. Not everything is about something Charlie.”

“Castiel,” she said in mock horror, “how dare! Without the minutiae of everyday existence, I would whither and die.”

“She would,” intoned Dorothy, without looking up from her phone.

Cas sighed and turned away to stare out the window hoping Charlie would take the hint and leave it alone. He saw her out of the corner of his eye giving him one last fond smile and turn the radio up.


	3. Chapter 3

**Notes for the Chapter:**

> I wrote some smut!

That night Cas had a dream.

_The sheets were twisted around him. There was a body with him- hard muscles and sweat-soaked skin. He licked at the chest, catching a nipple between his teeth and nibbling, causing a deep moan from its owner. Hands ran all over Cas’s body, a light lover’s touch, pressing in spots that caused him to quiver. The sheets were billowing about them, blocking his view of who he was rolling around the bed with, but he felt it when a hard heat pressed up against his inner thigh. It was his turn to moan as he thrust his hips to press on the heated flesh. Cas ran his hands down the back and over the globes of a very perky ass and grabbed two handfuls and squeezed while thrusting again. He felt his own throbbing erection slot against the mystery man’s and they began to move in sync-_

Cas woke up with a gasp and a raging hard-on. He already had a hand stuffed down his pants in his sleep, and was gripping himself and rubbing. 

It clearly had no intention of going away.

Cas looked at the clock. It was still 45 minutes until he had to be up so that was plenty of time. He rolled to the right to fish under his mattress for the small bottle of lube he kept there. His fingers found it, and he rolled back and slid off his pajama bottoms under the covers. His sheets were a little damp with perspiration, so he’d have to change them anyway.

He poured a small amount of lube in his hand. It was cold and he winced as he slathered it on himself and rubbed it around to get it warmed. His erection had waned slightly while he was getting the lube, but after a few strokes, he was back in business. 

He threw the comforter over his head so he could watch; he always left his small desk light on at night in case he needed to get up. He watched as his hand rose and fell at a maddeningly slow pace, the slick sound he made amping up the pleasure. He closed his eyes and began to riffle through his ‘spank bank’ (Gabe called it that and for some reason Cas couldn’t refer to it as anything else). 

There was that guy at the downtown library the other day. He had smiled at Cas and his eyes lingered a little too long. He had short brown hair and eyes to match. _Cas went over to him and pulled him into a kiss._ That image was working. Cas sped his hand up a little. _Now Brown-eyes dropped to his knees and pulled Cas’s cock out, immediately sucking into his mouth, all the way down his throat. Cas gripped the table behind him and let the guy swallow him a few times and bob up and down. He needed something more. The scene switched and the guy was laid out on his stomach over the library table, legs spread and hanging off the end. Cas ran his dick along the crease of his ass, thumbing the guy’s already loose asshole. The guy moaned._ Cas moved the blanket off of him and flipped onto his stomach. He began rutting into his hand, simulating pressing into the guy slowly. _He felt Brown-eyes pushing back against him as he slid in, thrusting slowly only for a minute before really going to town on the guy; slamming into him making him groan out Cas’s name in a deep familiar voice. Cas reached around and felt the weight of the guys cock as it smacked against the underside of the table. The guy was rock-hard and drove his hips back harder, fucking faster onto Cas’s dick, making heat pool low in his belly, making his balls draw up tight against his body. Cas reached forward to grip the guy’s shoulder with his free hand to thrust deeper. The man’s head turned and Cas was suddenly looking into deep green eyes and reddened cheeks. “Cas,” he whispered._  
“Dean!” Cas cried out into his pillow, and came all over his hand and sheets, endorphin rush making him white out a little, his hips making shallow thrusts into the pool of come as he worked through the last of his orgasm. 

Fuck. That happened. Cas slowed his breathing and lifted himself on his elbows and peered down at the damage. There was a sizeable wet spot and his hand was pretty covered. He groaned and sat up, wiping his hand on the sheet. He was glad he had moved the comforter when he flipped, or it would have been more mess to clean up. Looked like he’d be doing laundry early that morning.

Doing laundry _and_ lamenting the fact that he just had an unintentional sex dream then fantasy jerk-off session to Dean Fucking Winchester. He shuddered thinking about the moment of climax- Dean looking back at him and whispering his name like that. _Fuck._ that was so hot. His dick gave a twitch of interest.

“This is all you fault,” he scolded his crotch, “you and your damn vivid imagination.”

His cock remained silent on the matter but supplied him with a few more images of Dean spread over the table, fucking back onto him.

“Fuck,” Cas whispered and fell back onto his bed directly into the wet spot.

 

*******

 

The day only went downhill from there. When Charlie came to pick him up for school, she was decked out in red and pink, and Dorothy was sharing a seat with an oversized stuffed bear. SHe kept looking over at Charlie with heart-eyes and Cas felt like vomiting. 

He had totally forgot that it was Valentine’s Day. 

He sighed a long-suffering sigh and closed his eyes, leaning his head against the window, trying to let the cold glass ground him to reality. His eyes popped open right away. Closing his eyes was a bad idea when remnants of his Dean Fantasy of Doom lingered behind his eyelids. He prayed that he wouldn’t run into him all day. If he could just erase him from his mind, he’d be alright.

“So, you thinking about Dean?” Charlie quipped suddenly.

Cas groaned. So much for that plan. “No, of course not, why would I be thinking about him, that would be the _last_ thing I would be thinking about right now so just drop it already.”

Dorothy twisted in her seat and pegged him with a smirk. “The lady doth protest too much me thinks,” she said with a chuckle.

“Ha ha ha,” Cas retorted with narrow eyes. But he could think of nothing further to add that wouldn’t make things worse.

Dorothy reached back and poked his knee, trying to tickle it. Cas squeaked and swatted her hand away, and they had a small battle of poking and loud barks of laughter until Charlie started shouting above them not to interfere with the driver or she would turn the car around and no one would get to go to Disney World. 

With one last poke in Dorothy’s side, Cas sat back in his seat as far as he could to keep out of her reach. She stuck her tongue out at him and turned back around. 

Cas loved his friends. He could always count on them to cheer him up.

But then he walked through the front doors of the school. 

Red crepe paper twisted across the front hall, taped up with bunches of balloons on each end. Pink and white and silver banners and cheap hanging signs sported cardboard versions of those chalky candy hearts with dumb expressions on them: “Be Mine,” “Too Cool,” and “Tru Luv.” Cas glowered in the general direction of the cheerleaders’ carnation table and was grateful that Naomi and her cohorts had graduated last year. But the newer ones were not much better and a few in his class, like Rebecca and Lisa, still remembered and would point and whisper as he walked by. 

He scurried to homeroom quickly and kept his head down until Mr. Singer’s class. It seemed like everywhere he looked, students were being delivered carnations: white for friendship, pink for flirtation, and red for love. It was depressing. Cas ignored everyone and kept his nose buried in a book that he wasn’t really retaining. 

His mind kept drifting back to Dean Fucking Winchester. 

Cas prayed that he wouldn’t run into him on the way to class again. Sort of. Well, it wouldn’t be a terrible thing, not really. Maybe he could just catch a glimpse of him from far away- _Geeze dude, you’re beginning to sound like a stalker._

The bell sounded and he grabbed his books and skirted the other kids and ducked out the door. He needed to cross through the front hall to get to his locker, but it meant going by the carnation table. It was totally a set up, but he needed to ditch a few textbooks, and there was no way around it. He just hoped he could get by them without incident. 

No such luck.

“Hey angel!” a voice called out.

Cas cringed and kept moving. That was Meg. She was a year younger and they had been friends once, but after she found he didn’t return her romantic feelings, she abandoned him. And when she became a cheerleader, she seemed to think she needed to prove that she was never really friends with him. He had a feeling it was about to get nasty.

“I’m talking to you, Castiel,” she taunted, “send any carnations this year? I have a few guys I’d like to get deported. Maybe you could chase them off by creeping on ‘em for me.” The girls around her tittered and a few looked uncomfortable. Cas had to stop because of the crowd buying flowers clogging up the hall. He thought it would be a good time for the floor to open up and swallow him whole. 

“Shut the fuck up, Meg,” came a voice from directly behind him. 

_Oh shit, not now!_

Of course when Cas turned around it was Dean Fucking Winchester, standing about a foot away. So close. Cas fought the wild urge to reach out and run his fingers down Dean’s chest to see if maybe he was still dreaming. 

“You shut the fuck up, Winchester,” Meg said angrily, “what, are you into dudes now that Lisa dumped you?” People were watching the exchange now, whispering to each other. 

Dean’s eyebrow shot up. “For the record, I broke up with her, _Lisa,_ ” he said pointedly. Lisa had the decency to look abashed. 

“And secondly, just because I dated a chick and play football doesn’t mean I have to conform to your ideal of sexuality. Now quit being a homophobic bitch and harassing people on Valentine’s day just because you’re alone and miserable.”

Cas could feel himself getting angrier and angrier. Dean turned back to Cas with a broad grin, apparently proud of himself for saving the poor little gay boy.

“I don’t want your pity, Dean,” he growled. Dean looked like he’d just been slapped.

“I-I didn’t mean-” he sputtered.

“I know what you meant. I can take care of myself.” Cas spun on his heel and marched through the crowd watching him. Thankfully, they moved to let him pass. 

Great. Now he had another thing that people would gossip about. His face felt hot with humiliation. He got his books, slammed his locker harder than necessary and stalked off to class. As he walked, he started to feel bad about the way he’d talked to Dean. Cas knew he meant well, had been kind to him out of pity, and he had shit all over his good deed. He supposed that was what guys like Dean did. Rescued the small guy and became the hero. There was nothing wrong with that, but Cas didn’t want that kind of attention. In fact, he wanted no attention, he wanted to get through the rest of the school year and head off to college where he could hopefully meet a few more people who weren't so small-minded. 

Cas sighed as he walked into Mr. Singer’s class. The least Cas could do was be grateful for Mr. Singer’s influence on Dean; at least the guy had been nice to him. 

“Mornin’ Castiel,” the teacher greeted him, “I got a chance to look over your essay, and I have to say I’m pretty impressed. It needs a little polishing, but it’s ready to get sent to Admissions. You still gunning for the Anthropology department?”

Cas smiled. At least he had some good news on this shitty day. “Yeah, and thanks for taking the time to read it.”

Mr. Singer chuckled. “It had some pretty funny parts in it. ‘Wears sensible shoes’ was definitely my favorite.”

Cas grinned. “Yeah, that one is pretty good. I also like ‘Confirmed Bachelor’. Or ‘is the gentleman Earnest’? But I always like Oscar Wilde references.”

Mr. Singer nodded and laughed. “In my day we had a few I found amusing. ‘Light in the loafers,’ or ‘friend of Dorothy.’”

“There were quite a few I didn’t add,” Cas said, ticking off his fingers, “Wears a Light Wristwatch, Upside Down Chimney Sweep, Rides the Carousel, He throws a party with an open guest list, and my personal favorite, Gives Too Much Change for a Dollar.”

Mr. Singer was laughing so hard he was coughing, confirming Cas’s belief that the teacher probably smoked when he wasn’t at the school. 

The other students were loud and talkative, not paying them any attention. They were mostly chattering about the stupid carnations and the stupid people who might have sent the secret admirer ones. Cas felt his mood sour again. 

Class went on, mostly with the students editing their papers and helping each other by practicing their critical analysis skills. Cas was teamed up with Kevin and was carefully going through Kevin’s paper on Maternal Influence in Asian-American Families. It was a lot of new information to Cas, and highly interesting, so he didn’t notice when the classroom door opened and the room silenced.

“Castiel Novak?” someone called from the doorway. Cas jumped at the twangy voice. It belonged to Benny, a redneck football player dressed in a toga and no shirt with fake red wings on his back. A plastic bow and arrow hung at his belt. 

Benny’s eyes scanned the room when Cas didn’t answer. “Ah, there ya are,” the big guy smiled and made his way through the desk and handed a very befuddled Cas a pink carnation. 

“Becky Rosen?” There was a squeal from across the room, but Cas barely heard as he stared at the lone pink flower in his hand. 

“Who’s is from?” Kevin said, leaning forward and turning the tag on it.

Cas peered down at the little swatch of paper which held only one word. 

_Sweetheart._ There was a little drawing of a hand (maybe an emoji wave?) to the left of the word. It held no other answers.

“What the hell?” he said when he had his voice back.

Kevin’s eyebrows shot up. “Any idea who that could be?”

“Not a clue,” Cas responded. Although he did have a clue. A pathetic act of pity clue. That asshole Dean Fucking Winchester sent a flower to him because he felt sorry for him. 

Dean must have done it as another heroic act for the Little Guy. 

Or it was Meg being a dick. But Benny, who was reportedly Dean’s best friend, had delivered it, and he was from the carnation table set up in the cafeteria. Benny had always been nice enough to him and didn’t seem to have an ulterior motive. Cas squinted at the football player as he made his rounds handing out carnations. He grinned and shrugged when they all had been given out.

“And none for Gretchen Weiners,” he quipped as he darted out the door. The class laughed and went back to their classwork.

Cas was still staring at the carnation in his hand. He wanted to throw it away, but he noticed how delicately he was holding it. If he wanted to throw it away, why hadn’t he gotten up to do it? Well, maybe it wasn’t Dean who got it for him. Maybe it was just someone mocking him. Until he had further evidence, he decided to keep the flower. He opened his bookbag and took out his trig book and pressed the flower between the pages. It wouldn’t do to be seen walking down the hall with it. 

Class was over soon after that and the students filed out of class. Cas wondered how much trouble he’d be in if he signed himself out as sick and went home for the rest of day. Dad probably wouldn’t make a big deal out of it.

Cas took a trip to the boy’s bathroom before his next class. He splashed water on his face and leaned on the porcelain and watched as the drips from his face run down to the drain. He reached blindly over to the paper towel dispenser and pulled a few out to dry his face. He could make it through the rest of the day as long as he kept his head down and didn’t run into Dean again. 

He wiped his face and gave a start. Of course Dean was standing right behind him, looking at him through his reflection. Cas spun around to find he was very much too close to him.

_Guy must have a thing about personal space._

“Hello Dean,” he said, trying to sound bored. Dean blushed and took a step back. 

“Hey Cas.” Dean gave a half wave and blinked.

Cas once again took note of the exact color of Dean’s eyes. The green was ringed with gold, and they were beautiful in the florescent light of the bathroom. A barrage of public bathroom scenarios flooded Cas’s mind. _Not the time ._

“Can I help you?” Cas asked, wincing when it came out too sarcastic. 

Dean’s gaze dropped. “I...I thought Benny had delivered you a flower and I wanted to explain-”

“No need, Dean. It was thoughtful, thank you, can we move on with our lives?”

“Oh.” Dean looked crestfallen. 

Cas felt his stomach dip. He didn’t mean to be such a dick to the guy. He must have truly thought he was helping Cas, somehow. 

Cas switched gears. “Hey Charlie has people over on Fridays for Taco Tuesday, maybe you could come hang out, since...I mean. Lisa and all.” _Stupid stupid stupid._

Dean’s eyebrows shot up. “Tacos, you say? Tuesday tacos,” he grinned. “They must be really good to have them on a friday.”

Cas was relieved that Dean chose to ignore the comment about Lisa. “Yeah, we used to do it Tuesdays, but we kept staying up too late so we moved it to Friday. The name stuck and we still call it that.” This was the most he’s ever said to Dean before and it was about fucking tacos. He almost hoped Dean would decline. 

“Sounds good-” 

“We watch movies too,” Cas rushed through, “I think we have to suffer through a couple of rom coms-”

“I know. Remember? Charlie invited me yesterday, in the car?”

Cas knew he should have paid better attention. “Oh,” he said dumbly. 

“I wasn’t sure if I was gonna come, but tacos. She didn’t mention tacos, and I could literally live off tacos. That and pie. Yeah pie and tacos… Okay, I’m going to go. See you after school? I got my Baby back in action today, so you could ride with me and Sam? I have to drop him at Bobby’s first, but then we can to Charlie’s.”

He looked so hopeful, Cas couldn’t say no. 

“Okay...I’ll meet you in the back parking lot?” Cas absolutely had _not_ looked for Dean’s Impala when they got to school that morning.

“Okay,” Dean said brightly. “See you then.” He left the bathroom just as the late bell rang.

Cas stood there, immobile, and contemplated the surreal moment he had just had with Dean Fucking Winchester in the bathroom at school. They were going to hang out.


	4. Chapter 4

**Notes for the Chapter:**

> Here's a lil' long-ass chapter which contains domesticity, tacos, and smut.

The rest of the day passed in a blur and Cas went through the motions, no longer caring about Valentine’s Day, but definitely freaking out about _riding in a car_ with Dean Fucking Winchester. 

Cas texted Charlie about the development.

< So I’m going to catch a ride with Dean to your house after school

Charlie> !!!!!!

Charlie> So like “catching a ride” is what the kids are calling it these days?

< No it’s not like that. Shut up. 

Charlie> come on! You like him, admit it.

< He’s… not unpleasant.

Charlie> OH MY GOD YOU LOVE HIM

< *shakes head at stupid friend*

Charlie> *squees in delight at awesome matchmaking skills*

< *sees absolutely no matches having been made*

Charlie> *shakes head at stupid friend*

…

Charlie> do you think he ‘wears a light wristwatch’?

Charlie> is he a ‘fluent swimmer’?

 

Charlie> an ‘evening botanist’? 

< I knew I should have never let you help me with my essay.

Charlie> lol 

< We have to drop Dean’s little brother off at home first, but then we’ll be there. 

Charlie> So you guys can make out before you get here?

< *ignores friend’s comment* so we should have pie with our tacos.

Charlie> Are we still talking euphemisms for gay? That sounds more like a lesbian thing

< BYE

Charlie> lol

 

********

Cas nearly fell on his face when he saw Dean leaning casually against his shining black Impala. The sky was still gray, but he seemed to contrast it- he looked vibrant and alive on a dead spring day. A few flakes had begun to fall.

Making his way carefully across the parking lot, Cas’s traitor horndog brain kept offering him images of Dean spread over the hood of that car, thighs apart, stroking his thick long cock and motioning Cas to join him-

_He really needed to get a grip. If he was going to be friends with this guy, he has to stop picturing him naked._

Dean finally saw him and broke into a grin and waved. He opened the passenger door for Cas and then ran to the other side and hopped in. Cas was a little surprised and slid in carefully. 

He wondered if this wasn’t an elaborate hoax perpetrated by the athletic department. _Why was Dean being so nice to him?_

The car was already warm, and Cas relaxed into his seat as they pulled out of the parking lot. 

“Do you mind some tunes?” Dean asked as he fiddled with an ancient-looking tape deck mounted in the dash.

“No, not at all.”

Dean popped a cassette tape in and turned it down. When the music started it was still loud, which meant Dean probably listened to it at full volume.

The first strains of _Freebird_ started. Cas laughed out loud at that.

Dean looked affronted. “You don’t like Skynyrd?”

Cas waved a hand and waited his giggles out. “No I actually really like Lynyrd Skynyrd. My brother Gabe is into classic rock and plays it on his guitar.”

“Oh well, that’s cool,” Dean smirked, “I like him already.”

“You say that now,” Cas said, rolling his eyes. _Wait, what?_

Cas wondered what the _hell_ that meant. 

They pulled into the pickup line at the junior high school. Cas supposed this was where Sam went to school.

A tall, gangly kid came jogging over to the car, grin on his face. He hopped in the back and slammed the door.

“Watch the door, bitch!” Dean scolded him.

“Nice to see you too, jerk,” Sam said easily. He leaned forward and offered a hand to Cas.

“So you must be the famous Castiel,” he said, smirking in Dean’s direction.

“Seatbelt,” grumbled Dean, his face slightly turning pink.

“My Uncle Bobby talks about you all the time,” explained Sam.

“Good things, I hope,” Cas responded curiously.

“All good things, for sure,” Sam assured him. “I hope you don’t mind but he let me read your essay. It was really good. You have an excellent writing voice.”

 

Cas was impressed. But then again, the kid was being raised by Mr. Singer. 

“Why thank you,” Cas said smiling. “My dad’s a writer. I always had help on projects my whole life, but this one was all me.”

“Cool,” Sam said, “Dean read it too.”

Dean definitely turned red.

“We googled different slang for gay. Some of them were so-”

“Sammy that’s enough!” Dean interjected. “I’m sorry, Cas, Bobby was just so proud of how good you’ve done in his class, and he wanted to show off your essay.”

Cas chuckled. “That’s a huge compliment coming from him. I hope KU has the same reaction.”

There was a brief silence which threatened to become awkward. Cas could see Dean watching him out of the corner of his eye. 

“We’re gonna drop off Sammy-”

“It’s Sam, Dean, I’m not 12.” 

“We’re going to drop off Sam first, you should come say hi to Uncle Bobby and Rufus.”

“Oh, okay,” Cas was interested to see where they all lived.

He was surprised when they pulled in past Rufus’s shop and down a driveway in the back. Old junked out classic cars lined the gravel driveway which gave way to a small field and a large house set into the back of the property. 

Dean rolled to a stop and threw the car into park leaving it running. Cas corrected himself. _Her. He left her running._

They were soon at the door, which was unlocked (in fact, it looked like it may never have ever been locked), and Dean pushed it open and shouted for Mr. Singer- Bobby. 

There was a responding shout from the left. The room Bobby was in was stuffed with more books than Cas could count, there was a wide desk taking up the end of the room, a ratty couch and chair, and the man himself, kicked back at the desk, reading glasses slipped on his nose and a tumbler of an amber liquid in his hand. Cas grinned. He looked like a frog in a pond. He almost wore the room as a garment around his shoulders. It smelt of whiskey, burnt sage, coffee, and stale cigarettes. Cas noted a box of nicotine patches on the coffee table next to an ashtray. He loved this room.

“Hey there, my favorite student!” Bobby exclaimed as he looked up from the tome propped open on his desk. 

“Hello Mr.-”

“Call me Bobby here or it’s just weird.”

Cas smiled and nodded. “Bobby. You have a lovely home.”

Bobby snorted and looked around. “This crap heap?”

“Hey now, I take good care of this crap heap,” came a voice from the doorway. 

Rufus stood in the doorway drying his hands on a dishtowel. 

Bobby’s demeanor changed abruptly. “Yes you do, sweetheart, and I’m so very grateful for it.”

Rufus rolled his eyes. “Yeah, don’t even try to ‘sweetheart’ me, Bobby Singer, I’m still mad about the mess you made in the dining room.”

“I swear I’ll clean it up, I’m just in the middle of some very interesting research-”

“It’s all very interesting, isn’t it,” Rufus drawled as he walked behind the desk and planted a kiss on Bobby’s pouting mouth, “and I know you will clean it up before supper.”

Cas glanced at Dean who was leaning against the doorway, smiling at the exchange softly. Rufus walked by and nudged Dean with an elbow. 

“I know you’re involved in that mess somehow, so don’t think you’re out of hot water yet.”

Dean chuckled, “No Uncle Rufus, this was all Bobby.”

“Way to throw me under the bus, kid,” Bobby huffed. Rufus laughed and went back to the kitchen where some delicious smells were coming from. 

“Better watch it, Uncle Bobby,” Dean teased, “he knows you’d starve without him. And live in squalor.”

“God knows it too. That’s why I’m cursed to love him til the end of time.” Bobby sipped his drink and eyed Cas.

“Well, I guess you just got an eyeful there, didn’t you son?”

Cas felt like his cheeks were going to crack he was smiling so hard. “I guess so, Mr. S- Bobby.”

He was thrilled that he got to witness the exchange between Bobby and his… (Cas glanced at Bobby’s left hand) Husband! It was so great to see such a healthy relationship in someone his age’s home. Practically everyone he knew from school had divorced parents. Bobby caught him looking at his ring and held up his hand. 

“Fourteen years, can you believe it? That man has put up with me for _fourteen years._ I don’t know why he loves me so damn much.”

Dean chuckled. “You remember a gift for Valentine’s day this time?”

Bobby waggled his eyebrows. “You don’t even want to know.”

Dean groaned and covered his eyes. “Dammit Bobby why ya gotta- I have- we have company over!”

Bobby snorted. “Get over it. And go away. I’m waiting for Jess’s mom to come get Sam so those adorable lil’ lovebirds can have dinner together at steak n shake.”

“Jess is Sammy’s girlfriend,” Dean explained to Cas.

“She’s a sweet girl, and we like her alot,” Bobby said over his glasses. “Now if you could just find a-”

“That’s our cue to leave,” Dean said grabbing Cas’s elbow and practically shoving him out the door. Cas relished the contact. He swore he could feel the heat of Dean’s fingers through his three layers of clothing. They made it out the front door before Dean let go. 

They were silent for most of the way to Charlie’s. Dean turned down the music and looked over at Cas. 

“I’m sorry those guys give you such a hard time at school.”

“They’re your friends,” Cas responded.

“Hell no they’re not,” Dean said, “I just play ball with them. Benny’s my only real friend. And he doesn't hang out with them either. I just- I’m sorry I can’t stop them from being assholes.”

“It’s fine,” Cas said stiffly, “I’m used to it.”

“No, it’s not fine!” Dean exclaimed, hitting his steering wheel, “and I’m such a jerk standing by and doing nothing when those guys hurt other people who are just being themselves.”

“Dean,” Cas said softly, “they don’t need your pity.”

Dean whipped his head over and pinned Cas with a pleading look. “Look, it wasn’t pity, okay, I sent you that flower after I ran into you in the hall. Before Meg- I’m just- nevermind.”

Cas could almost see Dean raising walls between them. _What the hell was happening?_ Cas didn’t know what to say. He bought the flower before Meg taunted him- What did that even mean?

“Dean, I-” Cas frantically searched his brain for some way to show Dean he actually was flattered by the flower. He was flooded with relief that he didn’t throw it away. He pulled his bookbag up into his lap from the wheelwell and rummaged for his trig book.

Dean glanced over as he carefully opened the book, revealing the bloom carefully pressed with all the petals intact. It still looked fresh even though it was a little flat.

“You kept it,” Dean said surprised, “I thought you had thrown it away.”

“No!” Cas said quickly, “No, I would never- I mean no one’s ever given me a flower before and there was that incident… and I didn’t know if it was sincere.”

Dean cringed. “Yeah I should have thought of that, no wonder you were weirded out by it. It didn’t even occur to me. Benny had suggested I get you one when I told him… um. Yeah when I told him I thought you were… um. Nice.”

A smile crept its way across across Cas’s face. “Nice? You think I’m nice?” He decided to push his luck. “Nice enough to be called ‘sweetheart’?”

Dean definitely blushed. “I hope that wasn’t too forward.”

He could feel Dean looking at him, gauging for a response. Cas didn’t know what to say- the day had turned out very different than it had began. _Don’t think about the dream don’t think about the dream don’t think about-_ He tried to keep his face neutral as he willed his inappropriate boner not to make an appearance. 

Cas was rescued by pulling up to Charlie’s house. His dick surrendered in time to exit the car and enter Charlie’s house. The smell of tacos hit them in the face and Dean seemed to cheer up right away. He wasn’t kidding about his love of tacos. 

Kevin, Charlie, Dorothy, Cas, and Dean laughed and argued before settling on _10 Things I Hate About You,_ which fueled a discussion about watching other Shakespeare- related movies, like _Shakespeare in Love_ , which was not quite a rom-com, and _Much Ado About Nothing_ , which was the original rom-com.

Cas was stripped down to his button up and slacks, and was very aware of Dean’s eyes following him across the room. He settled in an arm chair to the left of the tv. Dorothy and Charlie claimed the couch, which left the floor for Kevin and Dean. Dean decided to sit right by Cas’s right leg, leaning against the arm of the chair. Cas could feel the heat radiating from his body and had to hold in a gasp. His fingers were so close to his head. He could almost touch the sandy light-brown hair- and run his fingers through it-

Cas shut that down. Now was not the time. 

The movie played, but Cas barely watched it. All he could concentrate on was the heat so close to his leg. He wanted to just inch his leg slightly and make contact. But what would happen? He could always get up and go to the kitchen and when he sat back down, move a little closer?

_God, what is wrong with you? The guy sends you a flower and now you’re scheming to rub up against him._

But he did have to pee. He sighed and stood quickly and went and peed, contemplating jerking off in the bathroom, decided to hold off until he got home, and headed back into the living room. 

Dean was now sitting in his chair. Dammit. Something he hadn’t thought of. He sighed and moved to sit where Dean had been, and was sad that he didn’t get to stare at the top of Dean’s head anymore. And an even more unnerving was having Dean stare at the top of his head. 

Cas sighed again and leaned his head back, resting it on the chair, annoyed with not having paid attention to the movie. It wasn’t hard to follow; he was very familiar with _The Taming of the Shrew,_ and the teen romance was reportedly based on it. 

Dean shifted in the chair, his leg moving to rest along Cas’s side. Cas froze. Was it unintentional? What should he do? Was this just casual touch? Or something else?

Cas breathed in slowly and held it for a few second before releasing it and relaxing his body, pressing back against Dean’s leg. He didn’t move it. Interesting. 

The movie droned on and they laughed and whistled at Heath Ledger and Julia Stiles’ awkward romance and the gratuitous slapstick. Cas had to admit it was pretty cute. Hardly the the “most important cinematic feature of our time” as Charlie claimed, but pretty cute. 

Cas suddenly felt fingers run through his hair. He leaned into the touch automatically before looking up to Dean in surprise. Green eyes met his blue ones; and a small shy smile played on Dean’s lips. Cas’s mouth twitched into a half smile in return and he turned back to the movie and let Dean comb through his hair. It felt really good. Cas had never had anyone do that for him. He was always running his own hands through, trying to tame its unruliness, but this was a completely different sensation. Calming. He sighed contentedly and closed his eyes to better feel Dean Fucking Winchester’s broad callused fingers stroke his scalp in a syncopated rhythm. The day had really been a rollercoaster. 

Cas woke to someone gently shaking his shoulder. “Cas, sweetheart, the movie’s over,” Dean was leaning down speaking into his ear softly. Cas turned toward his voice and found himself inches away from Dean’s face.

“How’d it turn out?” Cas asked absently, focusing on the plush lips in front of him.

The lips quirked into a smile. “After a few twists and turns and help from a few friends, they end up together in the end.” 

“Is that how it usually works?” Cas murmured back, “I really haven’t seen many of these movies before.”

Dean’s eyes flicked to Cas’s mouth as he spoke. “If it’s supposed to happen it will.”

Cas nodded, and nearly groaned in disappointment when Dean sat back up, taking his lush mouth and beautiful eyes with him. 

It became harder and harder to concentrate on the next movie with Dean’s hand back in his hair. Just the short conversation had Cas’s head spinning- he wanted to run away but also wanted to jump up and straddle Dean in the chair and suck on his lower lip. No one was paying them attention- well, Charlie had an eye on them, giving Cas a wicked smile every once in awhile. 

Dean’s hand disappeared and Cas immediately missed the warmth. Dean moved to the edge of the chair and slid down to sit next to Cas on the floor. He left his arm on the seat, close to Cas’s shoulders. Cas took the cue and naturally moved to rest against Dean wrapped in his right arm. Dean reached across and picked up Cas’s hand between them and laced their fingers together.

Cas had never cuddled anyone before. His sister Anna and he would still watch scary movies sometimes all snuggled up on the couch, and Charlie would drape herself over his legs when they did homework. But this was very different. It felt… tingly. Everywhere their skin touched felt like fire, and Cas could feel his pulse speed up. He wanted to touch more, and soon. Too bad they were in a room full of friends and Charlie’s parents would be back from dinner soon. Hell, he’d ravage Dean in a closet if he had to-

Cas reeled it back in and tried to calm himself. His position was hiding his erection, and he cursed his teenage hormones and lamented his lack of knowledge in that area. He wasn’t exactly a virgin; there was some dry-humping with another boy at church camp when he was 14, and that had resulted in mutual orgasms. But actual intercourse was still all theory (mostly porn) and no practice. He was at a loss and decided to just relax and enjoy the embrace of this interesting, hot guy who he had a bunch of preconceived notions about, but who was really great. And wanted to spend time with _him_ of all people. 

Dean’s steady breathing and warm body was lulling Cas back to sleep. It wasn’t long before Dean was gently shaking him awake again.

“Time to go, sweetheart,” he said, squeezing Cas’s hand a few times.

Cas blinked and yawned, giving in to the impulse to stretch out his back, popping it and groaning at how good it felt. He looked over at Dean, who was staring back with his mouth slightly open and eyes darting over his body. Interesting. Cas lengthened his body even more, preening under the attention.

“Okay there, Baryshnikov,” Dorothy’s snarky voice popped up, “now that you’re all stretched out, you can dance your ass right out the front door.”

Charlie broke into giggles as Cas scowled at the two of them. There was a choking sound beside him as Dean tried desperately not to laugh. Cas huffed and rolled his eyes in mock offense, stood and swung his scarf around his neck dramatically. He put his nose in the air and sashayed to the door. “Pip pip, Dean,” he sang out in a terrible British accent, “our carriage awaits.” He ducked and smiled when a few pillows flew his way along with a few cat calls and whistles from Kevin. Dean had a funny smile on his face and stood, bowing deeply and holding his hand out to Cas. He assumed that Dean would just take his hand and lead the way out the door, but once again Cas’s expectations were surpassed when he was spun expertly around and dipped. 

Cas lay in Dean’s arms, faces inches away. “Where’d you learn to do that?” He voice sounded breathy in his ears.

Dean chuckled and slowly unfolded the dip and returned Cas to a standing position. “My mom taught me to swing dance when I was a kid, and I don’t know, I just like it.”

“Well, you seem very adept.” Cas could already picture Dean in a zoot suit and fedora, swinging a chain and chewing a toothpick. _Down boy._

“Thanks, Cas, I really like it, and there’s this place where we could-”

“Alright, alright,” Charlie stood shooing the toward the door, “you don’t have to go home but you can’t stay here.”

They said their goodbyes and headed to the Impala. 

“You live far from here?” Dean asked, pulling out of the driveway.

Cas shifted uncomfortably in his seat. He honestly hadn’t thought that far ahead. “No, not exactly,” he said cautiously, “It’s kind of far- if you want, I can catch an Uber or something-”

“No, of course not, I’ll take you,” Dean said cheerfully. “Where am I going?”

Cas rubbed a hand down his face. Oh, fuck. He’d just lied. He started to panic a little. He decided to stall.

“Dean, can I ask you something?”

“Sure, Cas,” Dean said, pulling to the curb beside Charlie’s driveway. 

“Why?”

“Why what?’

“You know what I mean, don’t be obtuse,” Cas frowned. 

“I’m afraid I’m gonna need you to clarify,” Dean shot back.

“Why me? What the hell is going on? One minute I’m minding my own business, trying to get the fuck out of high school with as little drama as possible. The next thing I know, the most popular _jock_ in school buys me a flower and takes me out. Am I missing something here?” He looked over at Dean. The boy with the sandy brown hair and freckles, the beautiful smile and quick wit, was smiling softly with a undeterminable look. Cas wished not for the first time, that he could read people better.

“I guess I can see how you might be confused,” Dean said slowly, “but I assure you I am as shocked as much as you are to be here.” Cas opened his mouth to retort, but Dean held his hand up, his eyes begging for patience. Cas closed his mouth and nodded slightly. 

“I don’t know, man, I don’t wanna bore you with my whole life story, or whatever, and I’m not real good with words, so I’ll hit the high points. And the low points too.” He paused and looked down, a wry smile on his face.

“I grew up in a pretty liberal household. My dad was best friends with a gay man, and had been through the years of bigotry Bobby put up with. I know he meant well, but he would say he was grateful me and Sammy would never have to be treated that way. I looked up to my dad, and when I realized at an early age that I like both girls and boys, it was easier to just date girls and not worry about being hurt. 

“Anyway, flash to present, post-house fire and mid-football season when it all hit me. I had it all. The hot cheerleader girlfriend, friends, popularity, hell. I was a walking 80’s movie cliche. But I felt like I was missing something. Bobby had been hinting around that he knew what was going on, but I resisted. It was easier for everyone to think I’m straight and date girls than to worry about getting hurt when- when people find out. It didn’t matter; I am attracted to girls still, but I felt like a liar when I was with Lisa. She said she loved me, had our whole life planned out, but she didn’t even know me. Not really. I couldn’t trust her with that. And it hit me. Why would I be with someone I don’t trust? So I ended it with her Wednesday. She wasn’t happy, but didn’t seem too upset. I’m pretty sure she was cheating on me anyway.”

“I’m sorry,” Cas said automatically.

“No,” assured Dean, “I’m not sorry. I wasn’t happy. It needed to happen. And then…” he paused, and Cas could swear he saw Dean’s cheeks redden slightly. 

“And then I ran into you. Literally.” Dean chuckled and caught Cas’s eyes. “You have the most beautiful eyes, Cas. They remind me of the sky- Aaaand that was cheesy. Sorry.”

Cas grinned crookedly at him. “It’s funny, I was thinking the same about your eyes- not the sky thing, more of a fresh spring- okay yeah. I’m gonna stop right there. Please continue your story.”

A smirk slid across Dean’s mouth, causing Cas’s dick to twitch slightly in his pants. He was glad for his coat.

“Well, I don’t know, there you were, all flustered and pink cheeked, you glasses crooked on your nose,” Cas pushed them up automatically. “I just kind of knew...knew that I was still attracted to men.”

Cas rolled his eyes. “I’m hardly a specimen-”

“No, not like that,” Dean said quickly, “I mean, yeah you’re hot, but there was something else. I’ve known you for years, but we never were in each other’s circles, you know?”

Cas nodded. It was true; he had admired Dean from afar and somehow never had a class with him in four years. _Wait, did he say ‘hot’???_

“So anyway, I saw your paper, and contrary to popular belief, I’m not a dumb jock, and what I saw intrigued me. So I asked Bobby about you. He was so fucking excited. I had to chill him out- I was just asking about the paper- I wanted to read it.” He smiled sheepishly. “I know he’s not supposed to, but sometimes a essay crosses his desk and he insists that -if I won’t take his class- I need to see what I’m missing. I’m pretty sure that has a double meaning. 

“I read your essay that night, at home. I read it twice. I read it again, and it wasn’t just the words I saw on the pages, I saw _you,_ and I wanted to, I don’t know, get to know this guy with the snarky humor, amazing insight, and more Victorian names for gay people than possible. I guess, now that I think about it, the flower was probably a bad idea. I had forgotten about what happened with that English guy, and… I bought the flower off Benny after I told him everything that morning on the way to school. We have a daily phone call,” he explained. “He said to go for it, and he always seems to know what’s right, so I trust him. I wished he hadn’t started school here last year or he would have known sending a flower might not be good. The rest you know.”

Cas blinked himself out of the trance he had been in, watching Dean form words with those plush lips. He was listening, but damn those lips were distracting. He cleared his throat which was suddenly dry. “I’m not sure I do know the rest. Why sweetheart?”

Dean definitely blushed. “It’s from your paper- I had Benny write it because he can draw, and it had to look like a left hand…”

Cas burst into laughter. Dean grinned at him, clearly pleased. 

“Clever,” Cas said, wiping his eyes, “Left-handed sweetheart.”

“I thought so,” Dean said. “So now, where to? I need directions.”

Cas sighed. There was no way he could lie to Dean or even evade the topic of home.

“Okay, so it’s not far. I lied because I kinda feel weird about where I live.”

Dean shrugged. “No biggie, you’ve seen where I live, it couldn’t be worse than that.”

Cas cringed. “Not really what I meant, but I guess you’ll see for yourself.”

He gave directions to Dean whose eyes got wider and wider. He nodded and put the car in drive. The sat mostly in silence, listening to the Valentine’s Day songs on the classic rock station. There was a tense moment when Led Zeppelin's _Whole Lotta Lovin’_ got to the part of _I wanna be your backdoor man…_ and Dean snorted and they dissolved into giggles, breaking the tension. 

Soon they pulled into the circular driveway in front of Cas’s house. The outdoor spotlights highlighted the lush lawn and the fountain in front. The mansion- because that’s what it was- was set into the landscape, opulent and bright. An Escalade was parked out front with a licence plate reading “Angel.”

Cas really wished Gabe had parked his car in the garage. He was actually surprised he was here- Valentine’s Day was Drifter Christmas to him. Gross. 

Dean rolled to a stop and put Baby into park, letting out a low whistle.

Cas felt his face get hot. “I know, it’s ridiculous. My dad got published and then all this money was rolling in, then he got the whole book tour thing, and he just kind of went overboard. I don’t know how much he makes, but it still...I don’t know, makes me uncomfortable.”

“Well, you have to give me the grand tour, and I can judge for myself,” Dean clapped his hands and rubbed them together before hopping out of the car. Cas followed warily, hoping Gabe wasn’t anywhere around.

No such luck.

“Well, well, well, little bro.” Gabe strolled in decked out in a gaudy red tuxedo. “Your date for the night? Cas, I didn’t know you had it in you...or is it going to be in you?” he pointed his finger at Dean.

“Dean this is Gabe and he was just leaving,” Cas pushed his sawed-off asshole of a brother toward the door. Gabe went willingly.

“I got big plans for tonight, Kali is meeting me at the swinger’s club an-”

“Agh! I don’t want to know,” Cas shoved Gabe’s keys at him and opened the front door. 

Gabe waggled his eyebrows at Dean. “Don’t worry, handsome, no one else is home- Anna’s out of town, Mike has a dinner thing, and Dad’s on the road. The lube in in the bathroom-”

“BYE GABE,” Cas shouted, actually worried he was going to pass out from embarrassment. 

His brother was laughing hysterically as he slammed the door behind him. Cas took a few deep breaths and headed to the kitchen without meeting Dean’s eyes. “Let’s get something to drink. What’ll you have?”

“Do you have any beer?” Cas nodded gratefully. He hadn’t known if Dean drank, but it actually sounded like a good idea to have a beer to loosen up a bit. Cas wasn’t entirely sure what they were doing, but year, a beer sounded perfect. Or twenty beers.

He swung open the cocktail fridge embedded in the island. There were imports of Michael’s, but they wouldn’t be missed. He popped the top off two and handed one to Dean. The clinked bottles and drank. Cas had to stop himself from chugging it out of nervousness- he was a lightweight and didn’t want to suddenly ruin the night by throwing up on Dean’s shoes. 

They stood in companionable silence for a few moments, sipping their beers.

“Can I see your room?” 

Cas’s heart started thumping. _His dad wasn’t home and he had a boy in his room._ Talk about cliches. “Um, this way.”

The hallway was longer than it had ever been. They passed the second floor bathroom, which made Cas wonder in there was really lube in there. Didn’t matter, he had plenty in the-

Cas froze. He wasn’t sure how clean his room was, especially after his wild masturbation session that morning. He turned to Dean.

“Can I go in real quick and straighten up?” He tried to keep the panic out of his voice. Dean chuckled and bowed slightly, gesturing to the room. 

Cas rushed in and shut the door. He felt the room rock a little under his feet. _lightweight._ It wasn’t too messy. He quickly put on the fresh sheets and mattress cover he had left out that morning on the bed, glad the semen didn’t leak through the layers. He sniffed the air. Of course it smelled like a teenage boy’s room, he was a teenage boy. He arranged the pillows and dashed to the door to let Dean in. This was so odd. It was all new to him. 

Dean sauntered in, his usual confidence in place, and sat on the bed. He set his beer on the nightstand and turned to Cas.

“Cas, I don’t know what the hell I’m doing. I am completely new to this. I have never even kissed a guy and I’m kind of freaking out a little here, because I didn’t know we’d end up here tonight.”

Well that was unexpected. “I don’t actually have a whole lot of experience either. I mean, I’ve fooled around but I haven’t actually ever had sex-”

“Me neither,” Dean whispered.

Cas stared at him with wide eyes. “Really? But Lisa-”

“Yeah, we messed around but we never got...there. The trust thing, I guess.”

Cas shed his trench coat and jacket. He loosened his tie and sat carefully next to Dean. They were close enough for their shoulders to touch and knees to bump together. 

“You just met- got to know me today,” Cas said quietly, “how do you know you can trust me?”

“I don’t,” Dean said just as quietly, “but you already know more about me than most everyone I know. That’s… That’s sad, actually.” He huffed a laugh and took another swig of beer, emptying it. Cas looked down at his own bottle and downed the last few sips and sat it next to Dean’s, reaching across him and turning to face him at the same time. Cas could see the nervousness in Dean’s eyes. They were so innocent. 

“Dean,” Cas said, his voice dropping lower, “I want to kiss you now, can I?”

 

Dean breathed out in relief. “Oh god, yes.”

Their lips met awkwardly, until Dean turned to face Cas and removed his glasses and set them aside. He turned back and dove back in and their lips slotted into place. Dean tasted like beer, a little like taco seasoning, and something beneath that that Cas wanted to taste more of. Cas licked at Dean’s lower lip which opened immediately. Dean moaned into Cas’s mouth when their tongues met. Dean had his hands buried in Cas’s hair, running his fingers through it again and again. Cas was already working his hands under the hem of Dean’s shirt, ready to pull it over his head and get a look at those famous abs. Dean hummed and lifted his arms so the shirt could be removed, then his fingers went to Cas’s buttons, popping them quickly through the holes. Cas helped him along, pulling out his shirttail and breaking the kiss off again to remove his tie. They got to work quickly on belts and pants- Cas no longer worrying about going too fast- he had to touch more of Dean and right away. He slowly moved Dean backward up the bed as they kissed and panted, hands roaming and petting, fingers brushing pebbling nipples. They were soon lying next to each other only in their boxers, on their sides, slowing the kissing and stroking along their sides. 

“Cas,” Dean whispered, “what do you want to do?”

About a million images of all the things he’d like to do to Dean ran through his head in a split second.

“Dean, we will do whatever you want, go as far as you want. It hasn’t been long that you have come to terms with your sexuality, so-”

Dean laughed and pulled Cas closer, almost touching chests. Cas pulled him the rest of the way, humming when their bodies met, all the way to their erections brushing against one another.

“Don’t think for a second that just because I haven’t had sex with anyone that I am unfamiliar with...certain things.” Dean blushed and wrapped his arms around Cas and buried his face in his neck. 

“Oh, really?” Cas said teasingly, “so if I was to do this-” he ground their hips together, eliciting a gasp and a grind back from Dean. Their lips again with more fire than before and Cas’s hands wandered lower and lower until they rested on Dean’s round pert ass. Dean moaned and pushed back into Cas’s hands. 

_I will die a happy man if I’m right and Dean’s a bottom._

He squeezed Dean’s cheeks firmly, pulling them apart slightly. “May I-” 

“Yes, yes, oh yes,” Dean breathed out between kisses, “please. I want- please…”

Cas smiled against his mouth and slid his hands under the waistband of Dean’s boxer briefs. He dipped his hand in and ran a single finger down the length of Dean’s shaft. Dean shuddered and pushed into Cas’s palm. It was different to touch a dick that wasn’t his, to feel it throb against his hand. Cas ran his hand loosely over Dean’s cock, not providing much friction, but with enough pressure to make Dean pant into his mouth and whimper. _I want to hear more of those noises._

Dean was too far gone to return kisses, so Cas attached his lips and teeth to Dean’s neck and nipped lightly and sucked while increasing pressure to his strokes. Dean gasped and bucked forward into the channel of Cas’s fist, and Cas wondered if maybe this would just be enough. He could make Dean come, finish himself off, and call it a night. Dean was new to this, better not push it.

Dean fumbled his hand down to Cas’s to still it. “Not yet,” he panted, “I want to do more.”

Cas pulled his head back a little to look into Dean’s eyes. He saw nothing but confidence and lust and something softer floating just below the surface of those clear green eyes. Dean sucked his lower lip into his mouth and bit it lightly. Cas followed the movement, ducking forward to taste it for himself. “Of course, Dean, whatever you would like to try,” he said, “tell me what you want.”

Dean’s eyes darted to the side, suddenly shy. He tightened his grip around Cas’s waist and moved his other hand to encircle him. His cheeks grew pink and he hid his face in Cas’s neck, mumbling something Cas didn’t quite catch.

“I’m sorry, what was that?”

Dean huffed and pulled back slightly and sighed. “I want- just let me back up a little.”

Saddened, Cas tried to move backwards to give Dean some room.

“No! Not like that, I mean-” Dean sighed and pulled Cas even closer, throwing his leg up over Cas’s thigh. “I mean I like...I like it when I...when I’m, um, filled up.” Dean paused, not moving, waiting for Cas to respond. Cas continued to trace small circles on Dean’s back to soothe him. He waited.

Dean cleared his throat and continued. “I mean, I’ve done it before- I mean I’ve fucked myself before…” Cas couldn’t help the moan that escaped his lips and his hips grinding against Dean’s on their own. He tried to get ahold of himself so Dean could continue. 

“I like the idea of sex- being the one on top, being inside someone, and I’d like to try it, but...oh my god, I can’t believe I’m telling you this, but when we ran into each other in the hall, I just wanted you to fuck me.” Cas’s breathing sped up. There was a distinct possibility he would come in his shorts just hearing Dean talk like that. 

“Cas, I know it makes no sense. I’ve been attracted to dudes before, but they were all hollywood stars. Tom Hardy, Chris Evans, Cumberbatch, you know, fantasies. I’d picture one of them when I jerked off sometimes, and I wanted to know what it would feel like from the other end.”

Cas was again amazed at how much Dean just trusted him with this intimate stuff.

“I ordered a- you know, a fake dick, on the internet and gave it a go. Didn’t know what I was doing, but I watched some porn a little bit, and I was able to do it. So what I’m saying is that I’d like to try that for real. With you. It’s actually kind of cool that you haven’t done anything like it either, so you won’t know if I’m terrible at it.”

“Dean,” Cas said breathlessly, rutting against Dean’s thigh mindlessly, trying to relieve the pressure a little. “I don’t think you could be terrible at it if you tried. But let’s take our time, and we’ll see where it goes.”

“I have no idea how you have so much control,” said Dean with a smirk, rolling his hips against Cas’s, “when all I want is for you to pound me into the mattress.”

Cas growled and pushed Dean onto his back. Dean laughed and folded his hands behind his head, his cocky smile still in place. Cas decided to wipe it off for him. The underwear had to go. 

He settled over Dean’s thighs and slowly pulled his boxer briefs down. He lifted himself and let Dean kick them of the rest of the way. Cas pushed Dean’s thighs apart and settled between them on his knees. He returned the smirk to Dean and stroked himself through his boxers. This was the first time Dean got a look at Cas properly. His smile faltered and his eyes widened as he moved his hands back down and rested them on Cas’s hips. Cas scooted up higher, making Dean push his legs open further. Dean reached out slowly and ran his fingertips along Cas’s clothed cock. Cas’s hips thrusted forward on their own, the heat of Dean’s hand on him felt better than he could have ever imagined. 

“Can I try something, Cas?”

Cas couldn’t speak so just nodded.

“Take those off and come kneel over by my side, by my head.”

Cas quirked an eyebrow and slid off his underwear. Dean sucked in a breath, finally getting a full view of Cas’s cock. Cas knew it was impressive in size and length, so he let Dean oogle for a few seconds before he threw Dean’s leg over to the side and crawled up to kneel by Dean’s pillow. His cock jutted out from his body, just inches from Dean’s plush lips. _Oh my god, keep it together, don’t just come all over this gorgeous guy’s face before I get my first blow job._

Dean grinned happily and took Cas in hand, stroking a couple times. “I wanted to see what it felt like to have a dick in my mouth, so I practiced on the fake one. I can go pretty deep, actually.”

Cas had to close his eyes against the visage of the body spread before him, hard leaking cock resting on his belly, muscular from football, hand touching, and oh- other hand gently fondling his balls now. But when he closed his eyes he only saw Dean sucking a dildo while fucking himself back on another one, sweaty and moaning. He wasn’t going to make it.

“Dean, stop,” he said and Dean stilled his hand immediately. Cas opened his eyes. Dean looked crushed and Cas captured his hand and wove their fingers together. 

“No, no, not like that. Oh my god I want nothing more for you to take me in your mouth,” he shuddered and looked away. “But I’m am already about to come and I don’t want it to be over before I can make you come.”

Dean sucked in a small breath. Cas looked back at him. His eyes were so blown out that you only could see a sliver of green around them. Beautiful.

Dean moved his hands back to Cas’s thighs and waited while Cas took several deep breaths. He had to fight fire with fire. He quirked an eyebrow and looked down at Dean.

“You know I thought about you this morning. In my dreams,” he said, “and when I woke up, I fucked my hand and thought of you. I didn’t mean for that to happen, but Jesus, Dean,” he paused and shook his head. Dean’s grip on Cas’s thighs tightened. Cas began to reach down and run his fingers down that washboard chest. “I don’t know if I believe in fate, or whatever, but to be here with you right now, it just...I don’t know.” Dean nodded and knitted his eyebrows together. Cas smiled sweetly and moved Dean’s hand back over to cup his sack. Dean moaned and writhed on his back. He grabbed a second pillow and shoved it under his head to get better access to Cas’s cock. His first tentative lick had Cas reeling. Dean ran his tongue around the crown of his cock, flicking at the slit and tasting the precome that was dribbling out. Dean kept the hand not on his balls on Cas’s hip and pulled him slightly forward until just the head slipped through Dean’s lips. He groaned and was grateful that Dean was guiding his hips or he would have surely gagged him. Dean’s mouth was wet and firm as he pushed Cas forward and further in. ANd then further. He saw Dean concentrate and relax his throat and take him even further. Cas’s thighs were shaking so hard he had to grip the headboard. The Dean pushed Cas’s hip away, sucking hard as he did, causing Cas’s eyes to roll back. Then Dean got serious about it. Cas made all sorts of odd noises, and maybe he should have been embarrassed about it, but it seemed to just spurn Dean on, thrusting Cas faster and faster, until he was pretty much fucking Dean’s mouth. Dean had moved the hand on Cas’s balls through his legs to grip his ass and push him in and out, the hand formerly on Cas’s hip was now rapidly stroking himself. Dean moaned and Cas almost came right then. He had to think of some disturbing imagery just to keep from coming. _Dean gets off on this. Gets off from sucking my dick._

Cas curved slightly over and placed his hand on Dean’s and they jerked him together. Dean mumbled around Cas’s cock. “What about 69?”

“Oh,” said Cas, “yeah, okay let me-” He twisted and straddled Dean’s face, putting his face hovering over Dean’s swollen and throbbing cock. Cas’s mouth watered, literally _watering_ at the sight of Dean humping at the air, seeking friction. Cas pumped Dean a few times, wondering if he should dive right in or lick it a little. Dean took Cas into his mouth again, this time at a different angle. It felt so fucking good. Dean sucked but the angle was awkward. “Lay on our sides?” Cas suggested. Dean hummed in response and the shifted to their sides. Each spread their top leg up so the other could have access. Cas took Dean in hand again just as Dean swallowed him down. He decided to put Dean out of his misery and put his cock in his mouth. Dean bucked a little and moaned, making Cas moan, and they began moving in tandem. Cas realized that if he did something to Dean’s cock, Dean would mimic the movement. It was distracting and kept him from coming too quickly. _Perfect._

He popped off Dean and sucked two of his fingers into his mouth, wetting them thoroughly. Dean moaned again, knowing what Cas was about to do. Cas had opened himself up before, and tried to find his prostate, and got up to two fingers before his brother almost walked in on him. He was sure he could make it good for Dean. He ran his sloppy wet middle finger along Dean’s paranium and down to his puckered hole. Dean pulsed in response, and pushed against Cas’s finger. _Oh my god he wants this so bad, wants me, how did I get so lucky?_

Cas rubbed in a circle, adding pressure until he felt Dean relax and then he pushed in. Dean gasped around his mouthful of cock, and he took Cas deeper in his throat. Cas pushed his finger deeper in response, feeling Dean bear down slightly to take it painlessly. He really knew how to take it up the ass. Cas pushed in further and began pumping in and out. Dean was going faster on Cas’s cock, and now had his thumb and forefinger tightly around the base of Cas’s cock, stemming the blood flow and preventing him from orgasming. Cas twisted his finger and searched around for the little knot of nerves. He brushed it’s edge, and by Dean’s cry, he knew he didn’t need to touch it again, or he would come. Cas would probably come too. He decided to stretch Dean instead. See how wide he could stretch him open, how many fingers. That might be fun. 

Cas kept his finger still and leaned up to rummage around under Dean’s pillow for the lube he had stashed there when he made the bed. Dean’s mouth was still full of cock, his eyes watering from his jaw stretched so wide for so long. The sight of Dean’s red, stretched lips around him was beautiful. He never wanted this to end. But he lowered himself again and started moving his digit again. Dean’s hole seemed to suck it in, greedy for penetration. Cas shuddered when he thought about slipping inside Dean, draped over his body, fucking into him. He stopped that train of thought. 

He managed to get the lube open with his teeth and squeezed too much on his hand and Dean’s thigh. The cold made Dean twitch, so Cas warmed it by slathering it on Dean’s dick and lightly stroking as he pulled back his middle finger and pushed it back in with his index finger. Dean groaned again, but showed no signs of pain. Cas pumped in and out, twisting and pulling on his rim, all the while wondering what it would be like to eat Dean out. _Next time._ He’d never considered it before, but he suddenly knew he had to try it on Dean. Make him feel so good. Fuck him with his tongue- He had sqeeze his eyes shut from seeing Dean’s hole swallowing his fingers so well. He slowly added a third. Dean had quit sucking Cas, and was just holding him in his mouth with his thumb maintaining the pressure to keep Cas from coming. Dean was breathing hard through his nose, and it was huffing across Cas’s balls, giving him goose bumps. 

Cas twisted the three fingers, Dean relaxing and pushing back quickly. Dean pulled off of Cas’s cock with a slurp. “Cas I need you to fuck me oh my god, I can’t stand it, I need you to fuck me, please.”

Cas looked up and saw the desperation. “Well if you’re sure,” he teased, “I can accommodate.”

Cas pulled his fingers from Dean’s red, stretched, wet hole and they sat up. “How do you want to do this Dean?” 

Dean shrugged. “Um, on my back? I kind of want to look at you and watch, you know.”

Cas nodded, and got between Dean’s legs. He had seen this one porn that he really liked and had watched several times, and he positioned Dean’s legs like that. Legs over his shoulders, bent in half, exposing his loose hole. Dean pulled Cas forward further, and just barely met lips, gentle presses, sweeter than before, almost tender. Cas pulled back and looked down at the man who was about to take his virginity, and who he would take as well and paused. It struck him suddenly how important this moment was. How significant that all the events of the past two days had lead them to this moment, hovering together on the brink of something new. 

Dean must have been having a similar moment when he spoke up. “Wow, this is really going to happen. I never would have thought- I’m so glad it’s with you, Cas.”

Cas smiled sweetly and pressed their lips together again. “Me too, Dean.”

Dean nodded and Cas put the swollen sensitive head of his cock against Dean’s entrance. He slowly added pressure until the head popped through the tight ring of muscle. Dean hissed in a breath, so Cas stopped, searching Dean’s face and eyes. He was so tight and hot, hotter than Cas thought possible, much hotter than if felt on his fingers. Dean hummed and nodded. “Keep going.”

Cas pushed and Dean bore down again, and Cas slid in smoothly until his balls rested against Dean’s backside. They both panted, sweat beading on their forehead. Cas moved Dean’s legs down until the were around his waist and Dean locked his ankles behind his back. Cas was suddenly able to reach Dean’s mouth again. The kisses started soft, but became heated quickly, tongues licking and sucking, Dean’s hands running all over Cas wherever he could reach. Dean started rolling his hips. Cas moaned and attached his mouth to Dean’s neck again. He pulled out and Dean started babbling nonsense words and curses as he pumped back in. He felt Dean’s cock throb between them, still slick with lube, spurting dribbles of precome. Cas moved quicker, knowing it was going to be over quickly for both of them if he didn’t hurry. He shifted Dean again, canting his hips a little and _there,_ if his calculations were correct, he nailed his prostate. Dean howled, and sobbed in pleasure as he came, come bursting between them, hot and slippery. Cas felt Dean constrict around him once and he came with such force he whited out for a moment. Silence rang in his ears for a few seconds and he felt Dean pull him down and wrap his legs and arms around him tightly. He melted into Dean, unconcerned about the mess beginning to dry between them. 

Their breathing was slowly returning to normal, and Cas felt the chill in the room for the first time. He pulled out with pushed up on wobbly legs and looked around for something to clean up with. His towel was draped over the chair on the far side of his bed, and with only a little grumbling from a half-awake Dean, he snagged it and began to wipe them up. The towel being damp from his morning shower made quick work of it. He tossed it over to the hamper, missing, of course, and pulled his blankets up from the floor and covered himself and Dean. He pulled Dean halfway on top of him, Dean’s head resting on his heart. He ran his fingers through Dean’s hair and they drifted off.


	5. Epilogue

**Notes for the Chapter:**

> Thanks for struggling through that misspelled grammatical nightmare! I love you all <3<3<3

Cas could feel something warm and soft pressed up against the length of his back. His return to consciousness was slow, he hadn’t had such deep, dreamless sleep in so long. A hand slid around from behind him and settled on his chest. _Dean._ He couldn’t believe all that had just happened. Surreal. But the evidence was spooning him, so definitely real. He wove their fingers together and sighed happily. 

Dean mumbled something into his back. Cas turned slightly. “What was that?”

Dean cleared his throat. “I said good morning, sweetheart.” Cas snorted and that earned him a poke in the side, which caused a bark of laughter. Dean got up, hair all amiss and lips still red from last night and tackled Cas, tickling him. “Help, no,” Cas squeaked, “no, I’ll pee on myself, god I gotta piss so bad!” Dean relented and snuggled back into the bed. Cas saw something purple on Dean’s neck. 

He sucked in a breath between his teeth. A green eye popped open and peered at him. “What is it?” Dean asked warily.

“Um, I kind of, um, maybe gave you a few hickies last night?” Cas said sheepishly. 

Dean felt his neck curiously with his hand. “Hmm.” he said shrugging. “I guess everyone’ll know I’m your Valentine.”

Cas burst into laughter and reached for his glasses, slipping them on. Seeing Dean more sharply was nice. Especially with the way he was looking at him now.

Cas stood up shamelessly, half-hard and all, and sauntered to the attached bathroom. He peed and brushed his teeth, and rummaged for a new toothbrush under the sink. Was this what it was like? Waking up next to someone, being silly in the morning? Dean calmed about any doubt he had about it being a one-time thing with that “I’m your Valentine” remark. But did Dean know he felt the same way? He had to be sure. 

He stepped out of the bathroom, still nude and raced to the bed, shivering. Dean held up the blanket for him to slide in. Dean hissed when Cas’s cold skin made contact with his warm skin, but he gathered Cas up and held him gently. Cas sensed Dean’s worry. 

“Dean,” Cas began cautiously, “I want you to know that I would like to keep doing this- I mean not fucking, I mean, yeah fucking because that was awesome, but i mean other stuff. Like, I don’t know maybe, but i was thinking we could go to the prom together?” Cas felt stupid as soon as it came out of his mouth. It sounded better in his head in the bathroom. 

Dean turned Cas over and kissed his forehead. He was smiling. “Yeah, I was gonna ask you the same thing. I didn’t know if that was your scene. I’d thought of it yesterday at Charlie’s house. But I wasn’t sure if you even liked me that way yet.”

Cas beamed at him and moved in to kiss the marks on Dean’s neck. “I’ll take that as a yes. Yeah you’re right, it’s not my scene, but only because I wouldn’t have asked anyone. I think it’ll be fun. I like to dance too.”

Dean practically jumped out of bed. “Oh my god I have the best idea, but I have to pee. Hold please.” He walked quickly to the bathroom. Cas enjoyed watching Dean’s morning wood bounce as he walked. It made him harden rapidly. He lazily stroked it while he waited. He threw back the covers exposing himself to the room, and to Dean when he came back in. 

“Hey Cas, I was thinking-” Dean stopped short at stared. Cas was spread out like a cat, hand rubbing lazily over his hard cock, holding it upright so Dean could get an eyeful.

“God, Cas you're so fucking gorgeous. You’d never know under that coat and suit there’s all this-” he waved his hand around and shook his head. Cas watched in amusement as Dean’s dick began to swell and fill out. “I guess I’ll have to tell you my awesome idea later.” Then he jumped on the bed and pulled the covers over his head and laid on top of Cas. 

They traded lazy, slow handjobs, and then again in the shower. Cas was so happy he didn’t even care when he got teased by his brother when they went in search of breakfast. In fact, Dean managed to dodge Gabe’s remarks and get a few snarky jabs in, which earned him a place in his older brother’s heart. 

They had all Saturday to laze around, so they went to Dean’s to hang out until Rufus cooked them supper. Mr. Singer- Bobby looked very smug the whole time. He gave Dean a whole lot of I-told-you-so looks. Cas had a great time.

****

“Come on Dean, we have to leave now, Charlie and Dorothy are waiting and the limousine is by the hour.” Cas tried to tame his hair one more time and blinked his contacts around a little. He was still getting used to them. 

“Ba dun dun da!” Dean called as he stepped from Cas’s bathroom. The tuxedo fit him like a glove. Cas had had one of Michael’s old tuxedos fitted to Dean- of course Dean wouldn’t accept a new one. It fit smoothly across his shoulders and over his waist, deep blue vest and tie, looking sharp against his freckled skin. Cas stepped into his space. 

“You look good enough to eat,” Cas purred, “and I just might have-”

“I thought you were in a hurry, sweetheart,” Dean teased, reaching up and messing up Cas’s hair the way he liked it. He kissed Cas lightly, then deeply, and pulled back striding out of the room. Cas rolled his eyes and followed.

The prom was lame, as expected, but the highlight of the night was the East Coast Swing dance Dean had choreographed for the two of them. They slid around the dance floor, with ease, as if they had performed this dance together their whole lives. Their friends and others hooted and cheered, drawing others from around the room. Sure, there were a few uninterested parties that hung back, but the student body had adjusted better than they could have hoped for in the two months since they came out as a couple. 

And soon would be graduation and college for Cas. Dean wanted nothing more than to be with Cas and eventually take over Rufus’s Garage when his uncles retired. It was good work that made him happy. They had talked about moving in together, and even talked about their shared dream of having a family someday. 

Dean tugged Cas’s hand and reeled him in then twirled him into a spin, laughing and catching him. Cas was right on tempo and in sync with Dean, and perfectly happy.


End file.
